Lumiracoxib

Summary

Lumiracoxib (CHEMBL404108) is an approved small-molecule cyclooxygenase 2 inhibitor (ATC M01AH06) targeting PTGS2; indicated across 5 conditions including rheumatic disorder and rheumatoid arthritis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: M01AH06
• Targets: 1 (PTGS2)
• Indications: 5 conditions
• Clinical trials: 17
• Chemistry: 293.72 Da · C15H13ClFNO2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL404108
Name	Lumiracoxib
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	151166
ChEBI	CHEBI:73044
ATC	M01AH06
Molecular formula	C15H13ClFNO2
Molecular weight	293.72
InChIKey	KHPKQFYUPIUARC-UHFFFAOYSA-N

SMILES: CC1=CC(=C(C=C1)NC2=C(C=CC=C2Cl)F)CC(=O)O

IUPAC name: 2-[2-(2-chloro-6-fluoroanilino)-5-methylphenyl]acetic acid

ChEBI definition: An amino acid that is phenylacetic acid which is substituted at position 2 by the nitrogen of 2-chloro-6-fluoroaniline and at position 5 by a methyl group. A highly selective cyclooxygenase 2 inhibitor, it was briefly used for the treatment of osteoarthritis, but was withdrawn due to concersns of hepatotoxicity.

Pharmacological roles (ChEBI): cyclooxygenase 2 inhibitor, non-steroidal anti-inflammatory drug.

Also known as: COX-189, Lumiracoxib, Prexige, lumiracoxib, LUMIRACOXIB, SID144207115, SID170465597, LUMIRACOXIB (COX-189), LumiracoxibÊ, Lumiracoxib (COX-189), LumiracoxibÂ

Patent coverage: 5,050 distinct patent families (21,145 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 20,976 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
PTGS2	COX-2	Inhibition	6.49	0%	P35354

Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Peroxisome proliferator-activated receptor gamma, Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Nuclear receptor subfamily 1 group I member 3, Bile salt export pump.

Bioactivity

ChEMBL activities: 12 potent at pChembl ≥ 5 of 14 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS1	8.15	IC50	7	nM	CHEMBL_ACT_10908203
PTGS2	8.15	IC50	7	nM	CHEMBL_ACT_2069748
Q05769	7.4	IC50	40	nM	CHEMBL_ACT_13487884
PTGS2	7.22	IC50	60	nM	CHEMBL_ACT_16507593
PTGS2	7.02	AC50	96	nM	CHEMBL_ACT_25166705
PTGS2	6.97	IC50	107	nM	CHEMBL_ACT_2128862
PTGS2	6.89	IC50	130	nM	CHEMBL_ACT_2128886
PTGS2	6.85	IC50	140	nM	CHEMBL_ACT_16486570
PTGS2	6.85	IC50	140	nM	CHEMBL_ACT_2128887
PTGS2	6.5	Ki	320	nM	CHEMBL_ACT_2128937
NR1I3	6.26	AC50	550	nM	CHEMBL_ACT_25164337
PPARG	5.82	AC50	1500	nM	CHEMBL_ACT_25114038

Target pathways

Aggregated over 1 target gene(s): PTGS2.

Top Reactome pathways

8 total, by targets touching each:

Pathway	Targets	Genes
Synthesis of 15-eicosatetraenoic acid derivatives	1	PTGS2
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)	1	PTGS2
Interleukin-10 signaling	1	PTGS2
Interleukin-4 and Interleukin-13 signaling	1	PTGS2
Biosynthesis of DHA-derived SPMs	1	PTGS2
Biosynthesis of EPA-derived SPMs	1	PTGS2
Biosynthesis of DPAn-3 SPMs	1	PTGS2
Biosynthesis of electrophilic ω-3 PUFA oxo-derivatives	1	PTGS2

Dominant GO biological processes

GO term	Targets
prostaglandin biosynthetic process	1
response to oxidative stress	1
embryo implantation	1
regulation of blood pressure	1
response to nematode	1
response to selenium ion	1
positive regulation of vascular endothelial growth factor production	1
cyclooxygenase pathway	1
lipoxygenase pathway	1
positive regulation of prostaglandin biosynthetic process	1
positive regulation of fever generation	1
prostaglandin secretion	1
regulation of cell population proliferation	1
long-chain fatty acid biosynthetic process	1
positive regulation of nitric oxide biosynthetic process	1

Indications & clinical

Indications

5 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
rheumatic disorder	4	MONDO:0005554	EFO:0005755
rheumatoid arthritis	3	MONDO:0008383	EFO:0000685
osteoarthritis, hip	3	MONDO:0006629	EFO:1000786
osteoarthritis, knee	3	MONDO:0005416	EFO:0004616
osteoarthritis	3	MONDO:0005178	MONDO:0005178

Clinical trials

Total trials: 17.

Phase distribution

Phase	Trials
PHASE3	9
PHASE4	7
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00170781	PHASE4	COMPLETED	Efficacy and Safety of Lumiracoxib 400 mg Once Daily in Acute Flares of Gout
NCT00170898	PHASE4	COMPLETED	Safety and Efficacy of Lumiracoxib Versus Naproxen in Acute Musculoskeletal Pain
NCT00267176	PHASE4	COMPLETED	Safety and Efficacy of Lumiracoxib in Patients With Osteoarthritis and With Controlled Hypertension
NCT00333567	PHASE4	COMPLETED	Efficacy and Safety of Lumiracoxib 400 mg in Arthroscopic Knee Surgery
NCT00348491	PHASE4	COMPLETED	Efficacy of Lumiracoxib in Relieving Moderate to Severe Post-dental Surgery Pain, Compared to Both Placebo and Celecoxib
NCT00350155	PHASE4	COMPLETED	Video Capsule Endoscopy to Investigate the Safety and Tolerability of Lumiracoxib in the Small Bowel
NCT00419796	PHASE4	COMPLETED	Effects of Lumiracoxib and Ibuprofen on Blood Pressure and Urinary Eicosanoid Excretion in Osteoarthritis Patients With Controlled Hypertension
NCT00145301	PHASE3	COMPLETED	52 Week, International, Multi-center, Randomized, Double-blind, Double-dummy, Parallel-group Clinical Trial to Compare Retention on Treatment, Safety, Tolerability & Efficacy of Lumiracoxib 100 mg od, Lumiracoxib 100 mg Bid & Celecoxib 200 mg od in Pts With Primary OA of Hip, Knee, Hand or Spine
NCT00154219	PHASE3	COMPLETED	Efficacy and Safety Study of Lumiracoxib in Patients With Primary Hip Osteoarthritis
NCT00170872	PHASE3	COMPLETED	6 Week Open-label Trial With Lumiracoxib 200mg o.d. in Primary Knee Osteoarthritis or Rheumatoid Arthritis
NCT00267215	PHASE3	COMPLETED	Efficacy and Safety of Lumiracoxib
NCT00366938	PHASE3	COMPLETED	Efficacy and Safety of Lumiracoxib in Patients With Knee Osteoarthritis (OA).
NCT00367315	PHASE3	COMPLETED	Efficacy and Safety of Lumiracoxib in Patients With Primary Knee Osteoarthritis (OA)
NCT00475800	PHASE3	COMPLETED	Efficacy and Safety of Lumiracoxib in Patients With Primary Knee Osteoarthritis(OA)
NCT00476034	PHASE3	COMPLETED	Efficacy and Safety of Lumiracoxib in Patients With Primary Knee Osteoarthritis (OA)
NCT00637949	PHASE3	COMPLETED	Safety of Lumiracoxib in Patients With Osteoarthritis
NCT01481610	PHASE2	TERMINATED	Safety Study of Renal Function in Patients With Chronic Kidney Failure Taking Lumiracoxib or Diclofenac for Arthralgia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for aceclofenac, aspirin, diclofenac, dip	CPIC	CYP2C9

PharmGKB also curates 0 clinical and 3 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

201 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
FIDAXOMICIN	ChEMBL + PubChem	Phase 4 (approved)	PTGS2
3,3’,4’,5-TETRACHLOROSALICYLANILIDE	ChEMBL	Phase 4 (approved)	PTGS2
ABEMACICLIB	ChEMBL	Phase 4 (approved)	PTGS2
ACALABRUTINIB	ChEMBL	Phase 4 (approved)	PTGS2
ACEMETACIN	ChEMBL	Phase 4 (approved)	PTGS2
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	PTGS2
ACETYLCYSTEINE	ChEMBL	Phase 4 (approved)	PTGS2
ACRIVASTINE	ChEMBL	Phase 4 (approved)	PTGS2
AMODIAQUINE	ChEMBL	Phase 4 (approved)	PTGS2
AMPHOTERICIN B	ChEMBL	Phase 4 (approved)	PTGS2
AMSACRINE	ChEMBL	Phase 4 (approved)	PTGS2
ANISINDIONE	ChEMBL	Phase 4 (approved)	PTGS2
APOMORPHINE	ChEMBL	Phase 4 (approved)	PTGS2
ARFORMOTEROL	ChEMBL	Phase 4 (approved)	PTGS2
ASPIRIN	ChEMBL	Phase 4 (approved)	PTGS2
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	PTGS2
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	PTGS2
BEPRIDIL	ChEMBL	Phase 4 (approved)	PTGS2
BIPERIDEN	ChEMBL	Phase 4 (approved)	PTGS2
BROMFENAC	ChEMBL	Phase 4 (approved)	PTGS2
CALCIPOTRIENE	ChEMBL	Phase 4 (approved)	PTGS2
CALCITRIOL	ChEMBL	Phase 4 (approved)	PTGS2
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	PTGS2
CANNABIDIOL	ChEMBL	Phase 4 (approved)	PTGS2
CAPSAICIN	ChEMBL	Phase 4 (approved)	PTGS2
CAPTOPRIL	ChEMBL	Phase 4 (approved)	PTGS2
CARPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
CEFAZOLIN	ChEMBL	Phase 4 (approved)	PTGS2
CEFTIZOXIME	ChEMBL	Phase 4 (approved)	PTGS2
CELECOXIB	ChEMBL	Phase 4 (approved)	PTGS2
CEPHRADINE	ChEMBL	Phase 4 (approved)	PTGS2
CIANIDANOL	ChEMBL	Phase 4 (approved)	PTGS2
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	PTGS2
CRIZOTINIB	ChEMBL	Phase 4 (approved)	PTGS2
DAUNORUBICIN	ChEMBL	Phase 4 (approved)	PTGS2
DESERPIDINE	ChEMBL	Phase 4 (approved)	PTGS2
DEXIBUPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
DEXKETOPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
DICLOFENAC	ChEMBL	Phase 4 (approved)	PTGS2
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	PTGS2
DOBUTAMINE	ChEMBL	Phase 4 (approved)	PTGS2
DOXORUBICIN	ChEMBL	Phase 4 (approved)	PTGS2
EPINEPHRINE	ChEMBL	Phase 4 (approved)	PTGS2
ERGOTAMINE	ChEMBL	Phase 4 (approved)	PTGS2
ESFLURBIPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
ETODOLAC	ChEMBL	Phase 4 (approved)	PTGS2
ETORICOXIB	ChEMBL	Phase 4 (approved)	PTGS2
FLUPIRTINE	ChEMBL	Phase 4 (approved)	PTGS2
FLURBIPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
FLUVASTATIN	ChEMBL	Phase 4 (approved)	PTGS2
FOLIC ACID	ChEMBL	Phase 4 (approved)	PTGS2
GLAFENINE	ChEMBL	Phase 4 (approved)	PTGS2
HALOPERIDOL	ChEMBL	Phase 4 (approved)	PTGS2
HEXACHLOROPHENE	ChEMBL	Phase 4 (approved)	PTGS2
IBUPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
ICOSAPENT ETHYL	ChEMBL	Phase 4 (approved)	PTGS2
INDAPAMIDE	ChEMBL	Phase 4 (approved)	PTGS2
INDOCYANINE GREEN ACID FORM	ChEMBL	Phase 4 (approved)	PTGS2
INDOMETHACIN	ChEMBL	Phase 4 (approved)	PTGS2
IPRONIAZID	ChEMBL	Phase 4 (approved)	PTGS2